A Local’s Guide to Living in Leonardtown, Maryland

Written By Malcolm Lawson
Leonardtown, Maryland, is a charming and historic town located in St. Mary’s County. Known for its picturesque waterfront, Leonardtown offers a unique blend of small-town charm and modern amenities. With a rich history, vibrant community events, and beautiful surroundings, Leonardtown is an appealing destination for those considering moving to Leonardtown. This guide will provide you with all the information you need about living in Leonardtown, including the top attractions, parks, restaurants, schools, shopping, and neighborhoods.

Top Things To Do In Leonardtown

Port of Leonardtown Winery - Test

Living in Leonardtown means having access to a variety of exciting activities and attractions. From cultural experiences to outdoor adventures, there’s something for everyone. One of the top highlights is the Leonardtown Wharf Park, a beloved spot for locals and visitors alike.

The Leonardtown Wharf Park is a scenic waterfront park perfect for relaxing and enjoying nature. It offers walking trails, a kayak launch, and stunning views of Breton Bay. One visitor remarked, “A beautiful and peaceful spot to unwind and take in the views.”

Another must-visit is the Port of Leonardtown Winery. This local winery offers tastings of their award-winning wines, a lovely picnic area, and events throughout the year. A happy customer noted, “Great wine, friendly staff, and a lovely atmosphere. A hidden gem in Leonardtown.”

For those interested in history, the St. Mary’s County Historical Society provides fascinating insights into the area’s past. The museum features exhibits on local history, genealogy resources, and guided tours. A recent visitor commented, “An informative and well-organized museum with knowledgeable staff.”

Top Parks In Leonardtown

Thing to do in Leonardtown Maryland


Leonardtown boasts several beautiful parks, offering residents plenty of opportunities for outdoor recreation and relaxation. For more details on state parks in Leonardtown, Maryland, check the Maryland Department Of Natural Resources for more information.

Leonardtown Wharf Park is not only a top attraction but also a fantastic park. It provides a serene environment with walking paths, picnic areas, and a kayak launch. One reviewer said, “A wonderful place to relax, enjoy the scenery, and spend time with friends.”

Myrtle Point Park is another popular spot, offering hiking trails, a sandy beach, and beautiful views of the Patuxent River. This park is ideal for nature lovers and outdoor enthusiasts. A visitor mentioned, “The trails are well-maintained, and the beach is perfect for a summer day.”

Nicolet Park features sports fields, playgrounds, and a splash pad, making it a great choice for active individuals and families. A local parent noted, “The kids love the splash pad, and there are plenty of activities for everyone to enjoy.”

Top Restaurants In Leonardtown

Leonardtown offers a diverse selection of dining options, catering to various tastes and preferences. Whether you’re in the mood for casual fare or fine dining, you’ll find plenty of great choices here.

The Front Porch is a beloved local restaurant known for its delicious American cuisine and welcoming atmosphere. A diner praised, “The food is always fantastic, and the service is top-notch. A must-visit in Leonardtown.”

For those craving Italian, Kevin’s Corner Kafe is a top pick. This cozy spot offers authentic Italian dishes and friendly service. One customer commented, “The pasta is amazing, and the ambiance is perfect for a romantic dinner.”

If you’re in the mood for seafood, Blue Wind Gourmet is the place to go. This restaurant serves fresh seafood dishes and has a great wine selection. A happy patron said, “The seafood is incredibly fresh, and the wine pairings are excellent. Highly recommend.”

Top Rated Schools In Leonardtown

Public Schools in Leonardtown, MD - Niche

Schools are a major consideration for those buying a home in Leonardtown. The town is served by some of the best schools in St. Mary’s County, offering excellent education and a variety of programs for students.

Top High Schools In Leonardtown

Leonardtown High School is well-known for its strong academic programs and diverse extracurricular activities. The school offers advanced placement courses, sports teams, and various clubs, making it a great choice for students.

Great Mills High School is another top-rated option, known for its excellent STEM programs and supportive community. The school has a variety of advanced courses and extracurricular activities.

Chocticon High School offers a well-rounded education with a focus on both the arts and sciences. Students here benefit from a range of academic and extracurricular opportunities.

Top Middle Schools In Leonardtown

Spring Ridge Middle School is praised for its engaging curriculum and dedicated staff. The school offers a supportive environment and a variety of academic and extracurricular programs.

Leonardtown Middle School provides a dynamic learning environment with a strong focus on academic achievement and personal development. Students have access to various clubs and activities.

Margaret Brent Middle School is known for its rigorous academic programs and supportive staff. The school encourages students to excel both academically and in extracurricular activities.

Top Elementary Schools In Leonardtown

Leonardtown Elementary School is a top choice for young learners, known for its nurturing environment and strong academic programs.

Oakville Elementary School offers a diverse curriculum and engaging teaching methods. Students here enjoy a variety of enrichment programs and activities.

Banneker Elementary School is celebrated for its excellent teachers and inclusive community. The school focuses on creating a strong educational foundation for its students.

Shopping In Leonardtown

Leonardtown, MD Leonardtown Centre Retail • View Property - Juster Development

Shopping in Leonardtown is convenient and varied, with several top-rated centers offering a mix of retail stores, dining options, and services.

The Leonardtown Centre is a popular shopping destination, featuring a variety of stores and restaurants. Shoppers appreciate the convenience and selection, with one noting, “It has everything you need in one place.”

Another great option is the First Colony Shopping Center in nearby California. This center offers a range of stores, including specialty shops and big-box retailers. A review mentioned, “Great selection of stores and ample parking.”

For those who enjoy unique finds, the Olde Town Square is a must-visit. This quaint shopping area features charming boutiques and local shops. One shopper commented, “A lovely place to find unique items

and support local businesses.”

Top Employers In Leonardtown

Jobs in Leonardtown are diverse, with several large employers providing opportunities in various fields. The average salary in Leonardtown is competitive, making it an attractive place for professionals.

MedStar St. Mary’s Hospital is one of the largest employers in the area, offering jobs in healthcare, administration, and support services. The hospital is known for its competitive salaries and excellent benefits, with many positions offering $50,000 to $90,000 annually.

St. Mary’s County Public Schools also provides numerous employment opportunities, from teaching positions to administrative roles. The school system offers competitive salaries and benefits, with many jobs ranging from $45,000 to $85,000 annually.

Naval Air Station Patuxent River, located nearby, is another major employer, offering jobs in aviation, engineering, and administration. Salaries here are often between $60,000 and $100,000 annually, making it a great place for those in the defense and aerospace sectors.

Top Neighborhoods In Leonardtown

Living in Leonardtown, MD | Housing, Restaurants, Attractions | Long & Foster

Finding the right neighborhood in Leonardtown is essential to ensuring it meets your needs. Each neighborhood offers unique features and amenities, making buying a home in Leonardtown an exciting prospect.

Leonard’s Grant is a large, planned community with a variety of homes, from townhouses to single-family residences. The neighborhood features parks, walking trails, and a community center. The average home price here is around $450,000.

Singletree is another popular area, known for its convenient location and variety of housing options. This neighborhood is close to shopping centers and schools, with homes typically priced around $400,000.

Esperanza Farms offers a mix of affordable and upscale homes, making it suitable for various budgets. The neighborhood has good access to amenities and the Patuxent River. Home prices here average about $350,000.

Cost Of Living In Leonardtown

The cost of living in Leonardtown is relatively affordable compared to other parts of Maryland. The average home price is around $400,000, which is lower than the state average. Renting a home typically costs about $1,600 per month.

Utilities in Leonardtown are reasonably priced. The average cost of electricity is about $120 per month, water is around $50 per month, and internet services cost about $60 per month. These costs are competitive with national averages.

The average salary in Leonardtown is about $65,000 per year, which is in line with the state average. This makes living in Leonardtown an attractive option for those looking for a balance of affordability and quality of life.

Finding A Home In Leonardtown

If you are thinking about moving to Leonardtown and would like more information about the area, our team of local real estate agents would be happy to help! We can talk to you more about our real estate market here, go over the home-buying process, and answer any of your questions about Leonardtown. Just fill out the contact form below to get started!

Check Out These Latest Leonardtown Homes For Sale!

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